Lauryl pyridinium 2-(5-chlorobenzothiazyl)-sulfide



Patented May 29, 1951 UNITED STATES PATENT OFFICE LAURYL PYRIDINIUM 2 (5 CHLOROBENZO THIAZY L) SULFIDE Lester A. Brooks, Norwalk, Cnn., assignor to R. '1. Vanderbilt Company, Inc., New York, N. Y., a corporation of New York No Drawing- Original application February 7,

1947, Serial No. 727,273. Divided and this application May 31, 1950, Serial No. 165,370

As a general method, I prepare this new compound by reacting a lauryl pyridinium salt with -chloro-Z-mercaptobenzothiazole. The reaction is conveniently eiiected in aqueous solution. Dilution, when the reaction is effected in aqueous solution, is not important except that excess water involves a separation of a corresponding excess quantity of water to recover a dry product. Ihe reaction requires equal molecular quantities of the reactants. In aqueous solution, the reaction is a simple metathesis occurring at ordinary temperatures. When the reaction is efiected in aqueous solution, the product is separated from the aqueous salt solution in any con- ;venient manner.

For example, lauryl pyridinium 2-(5-chlorohenzothiazyD- sulfide can be prepared as follows: grams (0.05 mol) of 5-chloro Z-mercaptobenzothiazole is neutralized with 90 cc. of 0.5618 normal sodium hydroxide. The clear solution is then added to a solution of 14 rams (0.05 mol) of lauryl. pyridinium chloride dissolved in 150 cc. of water. An immediate precipitate forms and there is obtained by filtering a quantitative yield of a waxy yellow solid product.

I have also found that lauryl pyridinium 2-(5- chlorobenzothiazyl)-sulfide, for example, can be prepared by reacting equimclar quantities of sodium hydroxide and lauryl pyridinium chloride to form lauryl pyridinium hydroxide and then reacting this with an equimolar quantity of 5- chloro Z-mercaptohenzothiazole at moderately elevated temperature.

The new compound of my invention is an effective fungicide in very low concentrations. Specifically, this compound has exhibited its characteristic fungicidal activity against Aspargillus niger, Gymnosporangium y'um'perivirginicanoe, Chaetomium globOsum, Metarrhz'zium glutinosum and Penicillium. Of these organisms Aspergz'llus m'ger has in general proven most resistant and I have therefore chosen it to illustrate this special activity in the following table. In this table, opposite the name of the particular compound, I have indicated the minimum con-- Aspergillus niger MLD R Pamper Lauryl pyridinium 2-(5-chlorobenzothiazyl)sulmillion tide 50 3O Lauryl pyridinium 2-(5-chlorobenzothiazyl)- sulfide is slightly soluble in water.

My new compound is soluble in acetone, methyl alcohol, ethyl alcohol, isopropyl alcohol, methyl ethyl ketone, methyl acetate, ethyl acetate, the monoethyl ether of ethylene glycol and the monomethyl ether of ethylene glycol and is insoluble in straight run gasoline (-72 API) and in benzene and is slightly soluble in diethyl ether. In addition, my new compound is insoluble in carbon tetrachloride.

The new compound of my invention is of special value, for example, in application to textiles to render the textiles proof against mildew or other fungus attack. This compound is conveniently applied to textiles by dissolving it in acetone, diluting this solution with from 1 to 3 volumes of water per volume of acetone, dipping the textile in this acetone-water mixture or spraying it upon the textile, and drying the textile. Effective amounts of-the new compound in the range of from 0.01% to about 0.5% by weight on the textile can be deposited upon the textile in this manner. Textiles exhibit a, high retention for this new compound, perhaps because of its waxy nature.

This application is a division of my copending application Serial No. 727,273, filed February 7, 1947.

I claim:

Lauryl pyridinium 2-(5 ch1orobenzothiazy1) sulfide.

LESTER A. BROOKS.

REFERENCES CITED The following references are of record in the file of this patent:

Number 1 Number UNITED STATES PATENTS Name Date Baird Sept. 17, 1935 Sebrell Dec. 17, 1935 Baird Jan. 4, 1938 Cramer July 12, 1938 Minich Mar. 2, 1948 FOREIGN PATENTS Country Date Great Britain 1936 

